Azo dyes.



rotates.

sraras rarnnr onnion.

ERNST FUSSZENEGGER, or LUDWIGSHAFEN-ON-THE-RHINE, GERMANY, ASSIGNOR' To BAIDISGHE ANILIN a SODA FABRIK, or LUDWIGSHAFEN-ON-THE-BHINE, GER- MANY, A CORPORATION.

No Drawing.

To all whom it may concern:

Be it known that I, ERNST FUSSENEGGER, a citizen of the Austro-Hungarian Empire, residing at Ludwigshafen on the Rhine, Germany; have invented new and useful Improvements in Azo Dyes, of which the following is a specification.

I have discovered that T can obtain valuable azo coloring matters by treating, with 'phosgene, an azo compound which can be invention may be represented by the formula in which X means hydrogen or methyl or alkoxyl. -My new products are characterized by consisting of dark powders which yield carmine red solutions in water and blue solutions in concentrated sulfuric acid. They are insoluble in dye cotton red. ()n reduction with stan nous chlorid and hydrochloric acid they give rise to a para-para-diamino-diphenyl-urea body and 1.Q-diamino-8-naphthol-3.6-disulfonic acid. I

The following example will serve to illustrate further the nature of my invention, which, however, is not confined to this example. The parts are by 18.8 parts of paranitranilin in the usual manner with 30 parts of 30%. hydrochloric compound thus obalcohol and in benzene and,

weight. Diazotize Azo DYES.

Patented Oct. 2c; 1913.

Application filed June 7', 1913'. Serial No. 772,295.

acid and 6.9 parts of sodium nitrite, and allow the diazo solution to flow into a neutral solution of 34.1 parts of the monosodium salt of 2.S-amino-naphthol-3.6-disultonic acid. After'stirring for about 12 hours, if the combination is not complete, add sodium acetate until the excess of free mineral acid has been fixed and then continue stirring until a test portion shows that no uncombined diazo compound is present.

Precipitate the coloring matter by means of common salt and filter, it oil. Then in-.

troduce the coloring matter thus obtained into about 1,000 parts of'water and reduce the nitro group by means of 36 parts of sodium sulfid at moderate temperature. Then acidity with hydrochloric acid, salt out the product and filter it off. Then dissolve it in from 1,000 to 2,000 parts of Water containing an excess of sodium carbonate, filter to remove any sulfur and then, while maintaining the solution alkaline and at about 30 (3., pass a current of: phosgene into the solution until no unaltered monoazo coloring matter is contained therein.

The final coloring matter dyes cotton brilliant red shades of excellent fastness against the action of light and on reduction with stannous chlorid and gives rise to para-para-diamino-diphenylurea and 1.2-diamino-8-naphthol-3.6'disulfonic acid.

Now what I claim is I 1. The new azo coloring matters which can be obtained from a paranitranilin body, 2.8-amino-naphtl1ol-3.6-disulfonic acid and phosgene, which colorin matters consist, when dry, of dark powers which are insoluble in alcohol and benzene, soluble in water yielding red solutions and in concentrated sulfuric acid yielding bluesolutions, and which dye cotton red'shades, and, upon reduction with stannous chlorid and hydrochloric acid give rise to a para-para-diamino-diphenyl-urea body and LQ-diamino- S-naphthoL3.6-disulfonic acid.

2. The new azo coloring matter .which can be obtained from paranitramlm, 2.8-aminohydrochloric acid.

We M11 naphtlml3.6-disulfenic acid and phosgene, I phenyl-urea and 1.2-diamino-8naphthol-3.6- 16 which coloring mutter consists, when dry, of dlsulfonic acid. w

a dark powder which is insoluble in alcohol In testimony whereof I have hereunto set and benzene, soluble in Water yielding a my hand 1n the presence of two subscribing red solution and in concentrated sulfuric Witnesses.v acid yielding a blue solution, which dyes ERNST FUSSENEGGER. cotton red shades, and which upon reduc- Witnesses:

J. ALEG. LLOYD,

tion with stannous chlorid hydrochloric JOSEPH PFEIFFER.

acid gives rise to para-pdra-diamino-di- 

